sendmail relay refusing to use @outlook.com forward

0

I use my own sendmail box which has been forward email to a gmail address for a while.

Decided to switch to an outlook.com address and configured the sendmail server (via virtusertable table) to forward all email to blah@outlook.com instead.

However, all attempts are failing and the message bounce. mail.log shows:

Mar 16 02:29:07 www sm-mta[27615]: u2G1T4iN027611: to=<blah@outlook.com>, ctladdr=<from@address.com> (0/0), delay=00:00:02, xdelay=00:00:01, mailer=esmtp, pri=120372, relay=mx2.hotmail.com. [65.55.33.135], dsn=5.0.0, stat=Service unavailable
Mar 16 02:29:07 www sm-mta[27615]: u2G1T4iN027611: u2G1T7iM027615: DSN: Service unavailable

Any ideas what I should be looking into ?

Sending email from that server to blah@outlook.com fail in a similar fashion.

Could it be that somehow my sendmail server is on a blocked IP address?

is there a process to unblock things?

thanks

jyavenard

Posted 2016-03-16T01:50:48.827

Reputation: 125

Have you set it up to authenticate with name, password and use secure transport (port 465/587)? All modern email servers deny unauthenticated, unsecured smtp relaying. – Fiasco Labs – 2016-03-16T03:39:02.667

this relaying a domain I own, it is the MX server. You certainly don't want to require authenticated connection with a MX server ! – jyavenard – 2016-03-17T12:24:29.760

Your MX server must authenticate and send secured to the server it connects up to. And if you don't have that, you are locked out of sending. You need SPF records for your MX and it must have a trusted connection to another SMTP server, otherwise you are locked out as a spam source. Open relay, which is what you are trying to do, is no longer acceptable. – Fiasco Labs – 2016-03-17T15:57:55.610

it has nothing to do with open relay.. please stop posting you obviously have no idea what you're talking about. – jyavenard – 2016-03-17T21:29:07.067

Answers

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Microsoft had blocked my subnet.

Upon filling the form at http://go.microsoft.com/fwlink/?LinkID=614866 I received an answer within the hour that the IPs had been "Conditionally mitigated" and everything works.

jyavenard

Posted 2016-03-16T01:50:48.827

Reputation: 125

And in this case, Microsoft is allowing a sidestepping of the authentication through allowed exceptions, just don't relay any spam accidentally (via hacks or other infection), or other networks will blacklist the originating IP and server. – Fiasco Labs – 2016-03-17T15:58:53.863

Asked: 2016-03-16T01:50:48.827

Viewed: 554 times

Active: 2016-03-16T03:50:13.327